CN113549115A - Carbene metal osmium complex and preparation method thereof - Google Patents
Carbene metal osmium complex and preparation method thereof Download PDFInfo
- Publication number
- CN113549115A CN113549115A CN202110914612.1A CN202110914612A CN113549115A CN 113549115 A CN113549115 A CN 113549115A CN 202110914612 A CN202110914612 A CN 202110914612A CN 113549115 A CN113549115 A CN 113549115A
- Authority
- CN
- China
- Prior art keywords
- osmium
- hexafluorophosphate
- carbene
- carbene metal
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052762 osmium Inorganic materials 0.000 title claims abstract description 33
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 30
- 239000002184 metal Substances 0.000 title claims abstract description 30
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 title claims abstract description 30
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000010668 complexation reaction Methods 0.000 title description 2
- -1 osmium ion compound Chemical class 0.000 claims abstract description 31
- KHHOLOMEVBPRQY-UHFFFAOYSA-K trichloroosmium;hydrate Chemical compound O.Cl[Os](Cl)Cl KHHOLOMEVBPRQY-UHFFFAOYSA-K 0.000 claims abstract description 15
- 238000000746 purification Methods 0.000 claims abstract description 5
- 238000007039 two-step reaction Methods 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 4
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000009210 therapy by ultrasound Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000003446 ligand Substances 0.000 abstract description 8
- 238000011160 research Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000004696 coordination complex Chemical class 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 230000002159 abnormal effect Effects 0.000 abstract description 3
- 238000007036 catalytic synthesis reaction Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- LDBJPSXCPVJIGH-UHFFFAOYSA-N 9-methyl-8H-1,9-phenanthroline Chemical compound CN1C=C2C(N=CC=C3)=C3C=CC2=CC1 LDBJPSXCPVJIGH-UHFFFAOYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- LIWOTMUIBGAHKI-UHFFFAOYSA-N methylideneosmium Chemical class [Os][CH2] LIWOTMUIBGAHKI-UHFFFAOYSA-N 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a carbene metal osmium complex and a preparation method thereof, wherein the complex is a divalent metal osmium ion compound supported by two bidentate abnormal carbene ligands and two monodentate ligands, and is 9-methyl-1, 9-phenanthroline.The hexafluorophosphate, the osmium trichloride hydrate and the silver hexafluorophosphate are taken as raw materials and synthesized by two-step reaction. The invention is a novel skeleton metal complex, has novel structure, has potential research value in the aspects of catalytic synthesis, medicinal chemistry and material preparation, has convenient and easily obtained raw materials for the preparation method, simple synthesis method and convenient separation and purification, and is suitable for the requirement of large-scale industrial production.
Description
Technical Field
The invention belongs to the field of metal organic chemistry, and particularly relates to a carbene metal osmium complex and a preparation method thereof.
Background
Metal organic chemistry is used as a cross discipline of organic chemistry and inorganic chemistry, and mainly researches on design synthesis of metal complexes and application of the metal complexes in the fields of chemistry, materials and medicine. Taking the application in the field of medicine as an example, the metal complex has a unique spatial structure and has specific biological activity in the aspects of cancer resistance, sterilization, inflammation diminishing and the like. Among metal anticancer drugs, although platinum drugs have been widely used in clinical treatment, such drugs also have serious toxic and side effects and drug resistance, and thus, it is of great importance to research novel anticancer drugs. The osmium metal complex has a slower ligand exchange rate, a stronger pi-feedback effect and a spin-orbit coupling effect, and is considered to be the most promising non-platinum metal anti-cancer drug. Therefore, the development of novel framework metal osmium complexes provides more opportunities for drug screening and research in other fields.
Disclosure of Invention
The invention aims to provide an octahedral osmium complex supported by a carbene ligand and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
a carbene metal osmium complex, the structural formula of which is shown in formula (I):
further, the nuclear magnetic resonance data of the carbene metal osmium complex are1H NMR(300MHz，CD3CN)δ9.64(d，J＝4.8Hz，1H)，8.90(d，J＝6.4Hz，1H)，8.59(d，J＝6.4Hz，1H)，8.54(m，2H)，8.31(d，J＝8.4，1H)，8.22(dd，J＝7.2Hz，1H)，8.15-8.06(m，3H)，7.81(d，J＝7.2Hz，1H)，7.73(d，J＝7.2Hz，1H)，7.36(m，1H)，7.15-7.10(m，1H)，4.78(s，3H)，3.39(s，3H)，2.29(s，3H)。
A preparation method of carbene metal osmium complex takes 9-methyl-1, 9-phenanthroline hexafluorophosphate shown in formula (II), osmium trichloride hydrate shown in formula (III) and silver hexafluorophosphate shown in formula (IV) as starting materials, and carbene metal osmium complex shown in formula (I) is synthesized through two-step reaction;
further, the preparation method comprises the following specific steps of heating 9-methyl-1, 9-phenanthroline hexafluorophosphate and osmium trichloride hydrate in an ethylene glycol solvent for reaction under an anhydrous and oxygen-free environment, treating a reaction product, reacting the reaction product with silver hexafluorophosphate in an acetonitrile solvent, and finally treating and purifying the reaction product by silica gel column chromatography to obtain the carbene metal osmium complex.
Further, 0.2mmol of 9-methyl-1, 9-phenanthroline hexafluorophosphate and 0.1mmol of osmium trichloride hydrate were added to each 1.0mL of the ethylene glycol solution.
Further, the heating reaction temperature is 200 ℃ and the time is 20 h.
Further, the reaction product treatment process specifically comprises: after the heating reaction is finished, cooling to room temperature, adding ammonium hexafluorophosphate and deionized water, wherein the molar ratio of the ammonium hexafluorophosphate to the osmium trichloride hydrate is 4:1, the volume ratio of the deionized water to the ethylene glycol solvent is 4:1, carrying out ultrasonic treatment on the obtained mixed solution, filtering a liquid phase to remove the residual solid, dissolving the residual solid in dichloromethane, washing with water, and carrying out rotary evaporation on an organic phase to obtain a crude product.
Further, the reaction product is treated and then reacts with silver hexafluorophosphate in an acetonitrile solvent, and specifically comprises the following steps: adding silver hexafluorophosphate and acetonitrile solvent into the crude product, stirring for 12h at 70 ℃, cooling to room temperature, collecting the mixture, rotary evaporating and purifying by silica gel column chromatography.
Further, the molar ratio of the silver hexafluorophosphate to the osmium trichloride hydrate is 1:1, and the volume ratio of the acetonitrile solvent to the ethylene glycol solvent is 2: 1.
Further, in the purification process of the silica gel column chromatography, the eluent is obtained by mixing dichloromethane and acetonitrile according to the volume ratio of 5: 1.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention is a novel skeleton metal complex, has novel structure and potential research value in the aspects of catalytic synthesis, pharmaceutical chemistry and material preparation, and the preparation method has the advantages of convenient and easily obtained raw materials, simple synthesis method and convenient separation and purification, and is suitable for the requirement of large-scale industrial production.
Drawings
The accompanying drawings are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a drawing of the example carbene osmium complexes1H NMR spectrum.
FIG. 2 shows the single crystal structure of the carbene osmium complex of the examples.
Detailed Description
The invention is described in further detail below:
an octahedral osmium complex supported by a carbene ligand is a divalent metal osmium ion compound supported by two bidentate abnormal carbene ligands and two monodentate ligands, and is synthesized by two-step reaction by using 9-methyl-1, 9-phenanthroline hexafluorophosphate, osmium trichloride hydrate and silver hexafluorophosphate as raw materials.
The structural formula of the octahedral osmium complex is shown as (I):
the nuclear magnetic resonance data of the octahedral osmium complex are1H NMR(300MHz，CD3CN)δ9.64(d，J＝4.8Hz，1H)，8.90(d，J＝6.4Hz，1H)，8.59(d，J＝6.4Hz，1H)，8.54(m，2H)，8.31(d，J＝8.4，1H)，8.22(dd，J＝7.2Hz，1H)，8.15-8.06(m，3H)，7.81(d，J＝7.2Hz，1H)，7.73(d，J＝7.2Hz，1H)，7.36(m，1H)，7.15-7.10(m，1H)，4.78(s，3H)，3.39(s，3H)，2.29(s，3H).
The single crystal data for this octahedral osmium complex are:
the reaction equation of the preparation method of the octahedral metal osmium complex is as follows:
the compound prepared by the invention is a novel framework metal complex, has a novel structure, and has potential research values in the aspects of catalytic synthesis, medicinal chemistry and material preparation. The preparation method has the advantages of convenient and easily obtained raw materials, simple synthesis method and convenient separation and purification, and is suitable for the requirements of large-scale industrial production.
The present invention will be described in detail with reference to examples. It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict.
The following detailed description is illustrative of the embodiments and is intended to provide further details of the invention. Unless otherwise defined, all technical terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention.
Examples
An octahedral osmium complex supported by an abnormal carbene ligand and a preparation method thereof comprise the following steps:
the method comprises the following steps: 9-methyl-1, 9-phenanthroline hexafluorophosphate (II) (68.0mg, 0.2mmol, 2.0eq.) and osmium trichloride hydrate (III) (31.5mg, 0.1mmol, 1.0eq.) were charged into a Schlenk tube, vacuum was applied, argon was replaced three times, and 1.0mL of an ethylene glycol solvent was added. The solvent was heated to 200 ℃ under reflux for 20h, then cooled to room temperature, then ammonium hexafluorophosphate (65.2mg, 0.4mmol, 4eq.) and 4mL of deionized water were added, the mixed solvent was sonicated, the liquid phase was removed by filtration, the remaining solid was dissolved in dichloromethane and washed with water, the organic phase was rotoevaporated, and the volatile solvent was removed to give the crude product.
Step two: to the crude product was added silver hexafluorophosphate (252.8mg, 0.1mmol, 1.0eq.) and 2.0mL acetonitrile solvent, stirred at 70 ℃ overnight, cooled to room temperature, after which the mixture was collected by rotary evaporation and purified by column chromatography (eluent dichloromethane/acetonitrile volume ratio 5: 1), collecting the product by rotary evaporation to give a yellow solid (114mg, 60%). The nuclear magnetic spectrum of the compound is shown in figure 1 by nuclear magnetic analysis:1H NMR(300MHz，CD3CN) δ 9.64(d, J ═ 4.8Hz, 1H), 8.90(d, J ═ 6.4Hz, 1H), 8.59(d, J ═ 6.4Hz, 1H), 8.54(m, 2H), 8.31(d, J ═ 8.4, 1H), 8.22(dd, J ═ 7.2Hz, 1H), 8.15-8.06(m, 3H), 7.81(d, J ═ 7.2Hz, 1H), 7.73(d, J ═ 7.2Hz, 1H), 7.36(m, 1H), 7.15-7.10(m, 1H), 4.78(s, 3H), 3.39(s, 3H), 2.29(s, 3H). The main structure of the crystal is shown in figure 2 by X-ray single crystal diffraction analysis.
The embodiments described above are merely preferred embodiments of the present invention, and should not be considered as limitations of the present invention, and features in the embodiments and examples in the present application may be arbitrarily combined with each other without conflict. The protection scope of the present invention is defined by the claims, and includes equivalents of technical features of the claims. I.e., equivalent alterations and modifications within the scope hereof, are also intended to be within the scope of the invention.
Claims (10)
1. A carbene metal osmium complex is characterized in that the structural formula of the carbene metal osmium complex is shown in a formula (I):
2. the osmium carbene complex according to claim 1, wherein the osmium carbene complex has nmr data of1H NMR(300MHz,CD3CN)δ9.64(d,J＝4.8Hz,1H),8.90(d,J＝6.4Hz,1H),8.59(d,J＝6.4Hz,1H),8.54(m,2H),8.31(d,J＝8.4，1H)，8.22(dd,J＝7.2Hz,1H),8.15-8.06(m,3H),7.81(d,J＝7.2Hz,1H),7.73(d,J＝7.2Hz,1H),7.36(m,1H),7.15-7.10(m,1H)，4.78(s,3H),3.39(s,3H),2.29(s,3H)。
3. A preparation method of the carbene metal osmium complex according to claim 1, which is characterized in that 9-methyl-1, 9-phenanthroline hexafluorophosphate shown in a formula (II), osmium trichloride hydrate shown in a formula (III) and silver hexafluorophosphate shown in a formula (IV) are used as starting materials, and the carbene metal osmium complex shown in the formula (I) is synthesized through a two-step reaction;
4. the preparation method of the carbene metal osmium complex according to claim 3, which comprises the following specific steps of heating 9-methyl-1, 9-phenanthroline hexafluorophosphate and osmium trichloride hydrate in an ethylene glycol solvent under an anhydrous and oxygen-free environment to react, treating a reaction product, reacting the reaction product with silver hexafluorophosphate in an acetonitrile solvent, and finally purifying by silica gel column chromatography to obtain the carbene metal osmium complex.
5. The method for preparing the carbene metal osmium complex according to claim 4, wherein 0.2mmol of 9-methyl-1, 9-phenanthroline hexafluorophosphate and 0.1mmol of osmium trichloride hydrate are added to 1.0mL of ethylene glycol solution.
6. The method for preparing the carbene metal osmium complex according to claim 4, wherein the heating reaction is carried out at 200 ℃ for 20 hours.
7. The preparation method of the carbene metal osmium complex according to claim 4, wherein the reaction product treatment process comprises: after the heating reaction is finished, cooling to room temperature, adding ammonium hexafluorophosphate and deionized water, wherein the molar ratio of the ammonium hexafluorophosphate to the osmium trichloride hydrate is 4:1, the volume ratio of the deionized water to the ethylene glycol solvent is 4:1, carrying out ultrasonic treatment on the obtained mixed solution, filtering a liquid phase to remove the residual solid, dissolving the residual solid in dichloromethane, washing with water, and carrying out rotary evaporation on an organic phase to obtain a crude product.
8. The preparation method of the carbene metal osmium complex according to claim 7, wherein the reaction product is treated and then reacts with silver hexafluorophosphate in an acetonitrile solvent, and specifically comprises: adding silver hexafluorophosphate and acetonitrile solvent into the crude product, stirring for 12h at 70 ℃, cooling to room temperature, collecting the mixture, rotary evaporating and purifying by silica gel column chromatography.
9. The method for preparing the carbene metal osmium complex according to claim 8, wherein a molar ratio of the silver hexafluorophosphate to the osmium trichloride hydrate is 1:1, and a volume ratio of the acetonitrile solvent to the ethylene glycol solvent is 2: 1.
10. The method for preparing the carbene metal osmium complex according to claim 8, wherein in the purification process by silica gel column chromatography, an eluent is obtained by mixing dichloromethane and acetonitrile according to a volume ratio of 5: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110914612.1A CN113549115A (en) | 2021-08-10 | 2021-08-10 | Carbene metal osmium complex and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110914612.1A CN113549115A (en) | 2021-08-10 | 2021-08-10 | Carbene metal osmium complex and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113549115A true CN113549115A (en) | 2021-10-26 |
Family
ID=78105495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110914612.1A Pending CN113549115A (en) | 2021-08-10 | 2021-08-10 | Carbene metal osmium complex and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113549115A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3012260A1 (en) * | 2013-06-20 | 2016-04-27 | Kuraray Co., Ltd. | Metal complex including tridentate aminodicarbene ligand and hydrogenation reduction method using same |
| CN107286200A (en) * | 2017-08-07 | 2017-10-24 | 南京师范大学 | A kind of double-core aryl osmium metal complex and its synthetic method and application |
| CN111548372A (en) * | 2020-04-28 | 2020-08-18 | 常州工学院 | Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof |
-
2021
- 2021-08-10 CN CN202110914612.1A patent/CN113549115A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3012260A1 (en) * | 2013-06-20 | 2016-04-27 | Kuraray Co., Ltd. | Metal complex including tridentate aminodicarbene ligand and hydrogenation reduction method using same |
| JPWO2014203963A1 (en) * | 2013-06-20 | 2017-02-23 | 株式会社クラレ | Metal complex having tridentate aminodicarbene ligand and hydroreduction method using the same |
| CN107286200A (en) * | 2017-08-07 | 2017-10-24 | 南京师范大学 | A kind of double-core aryl osmium metal complex and its synthetic method and application |
| CN111548372A (en) * | 2020-04-28 | 2020-08-18 | 常州工学院 | Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108409747B (en) | Synthetic method of 2-aminoquinoline dihydrofuran compound | |
| CN102408453B (en) | Salicylaldehyde Schiff base binuclear cobalt coordination compound and preparation method and application thereof | |
| Huang et al. | Imidazole-directed fabrication of three polyoxovanadate-based copper frameworks as efficient catalysts for constructing C–N bonds | |
| CN108794370A (en) | A kind of preparation method for drawing sieve to replace Buddhist nun's intermediate | |
| CN101353357A (en) | Organo-tin compound, preparation and use thereof | |
| Labattut et al. | Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings | |
| CN114149470B (en) | Ruthenium nitrosyl (II) complex and preparation method and application thereof | |
| CN110078695B (en) | Quercetin derivative and preparation method thereof | |
| CN108521780A (en) | The method that one kettle way prepares bis-dicarboxylic diamino platinum (II) derivative | |
| CN106866525A (en) | For synthesizing (1R, 2S) shellfish up to the chiral induction agent of quinoline | |
| Rao et al. | Transformation of One-Dimensional Achiral Structure to Three-Dimensional Chiral Structure: Mechanistic Study and Catalytic Activities of Chiral Structure | |
| CN105504305B (en) | One kind contains 3（4 pyridines）Coordination polymer of pyrazoles propionic acid and preparation method thereof, purposes | |
| Herrera et al. | Optimized syntheses of optically pure p-alkene ligands: crystal structures of a pair of p-stereogenic diastereomers | |
| CN113549115A (en) | Carbene metal osmium complex and preparation method thereof | |
| Saper et al. | Synthesis of chiral heterobimetallic tris (phosphinoamide) Zr/Co complexes | |
| CN101696218B (en) | Method for preparing o-aminopyridine copper coordination compound | |
| Dias et al. | Sterically demanding methyl tris (pyrazolyl) borate ligands: synthesis and characterization of thallium (I) complexes supported by [MeB (3-(t-Bu) Pz) 3]− and [MeB (3-(Mes) Pz) 3]− | |
| Takjoo et al. | Effect of solvents in mixed-ligand supramolecular self-assembly architectures | |
| CN110872305B (en) | Fluorocamptothecin medicament derivative and preparation and application thereof | |
| CN102702236A (en) | Copper nitrogen complex and application thereof | |
| Sheen et al. | Synthesis of titanium-TADDOLate complexes containing bidentate nitrogen donors and the asymmetric ethylation of benzaldehyde | |
| CN111039767B (en) | Method for preparing deuterated aldehyde by using triazole carbene as catalyst | |
| Teng et al. | Two supramolecular complexes based on polyoxometalates and Co-EDTA units via covalent connection or non-covalent interaction | |
| CN106588984B (en) | A kind of preparation method of 6- phosphoryls substitution phenanthridines analog derivative | |
| Zhu et al. | Tunable morphology and the changeable catalytic property of layered scandium coordination polymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20211026 |